DEXTROMETHORPHAN Latest Revision: June 23, 2005
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1 DEXTROMETHORPHAN Latest Revision: June 23, 2005 H 3 CO H H NCH 3 NCH 3 1. SYNONYMS CFR: Not controlled (OTC) CAS #: Hydrobromide anhydrous: Hydrobromide monohydrate: Other Names: (+)-3-Methoxy-17-methylmorphinan Dextromethorphan hydrobromide Demorphan hydrobromide Ro /5 Benylin DM Canfodion Cosylan Hihustan M 2. CHEMICAL AND PHYSICAL DATA 2.1. CHEMICAL DATA Form Chemical Formula Molecular Weight Melting Point ( C) Base C 18 H 25 NO Hydrobromide C 18 H 25 NO HBr H SOLUBILITY Form C E W
2 Hydrobromide fs vss ps Base fs Vss C = chloroform, E = ether and W = water, VS = very soluble, FS = freely soluble, S = soluble, PS = sparingly soluble, SS = slightly soluble, VSS = very slightly soluble and I = insoluble 3. SCREENING TECHNIQUES 3.1. COLOR TESTS REAGENT Liebermann s Froehde 1 COLOR PRODUCED Black Blue-green 3.2. CRYSTAL TESTS REAGENT CRYSTALS PRODUCED PbI 2 -KOAc Bunches of serrated plates 1 H 2 PtCl 6 Feathery rosettes THIN LAYER CHROMATOGRAPHY Visualization Acidified Iodoplatinate Purple/violet COMPOUND Relative Rf Values System TLC5 System TLC18 System TLC6 Dextromethorphan Hydrocodone Methadone Morphine
3 3.4. GAS CHROMATOGRAPHY Method DXM- GCS1 Internal Standard Stock Solution (ISSS): 0.05 mg/ml tetracosane in chloroform:methanol (4:1). Standard Solution Preparation: Accurately weigh and prepare standard solutions at approximately 0.05 mg/ml using the above internal standard stock solution. Sample Preparation: Weigh approximately 20 mg into a GC vial (~2mL). Fill with ISSS. If necessary, filter sample through glass wool. Instrument: Column: Carrier gas: Agilent 6890 Series II (or comparable) gas chromatograph operated in split mode equipped with a FID detector 5% Phenyl/95% Methyl silicone gum 12 m x 0.2 mm x 0.33 µm film thickness Helium at 1.0 ml/min for 5 min ramped flow to 2.0 ml/min Temperatures: Injector: 270 C Detector: 280 C Oven program: 1) 175 C initial temperature for 1.0 min 2) Ramp to 280 C at 15 C/min 3) Hold final temperature for 4.0 min Injection Parameters: Typical Retention Time: Split Ratio = 60:1, 1 µl injection Dextromethorphan: 5.18 min Tetracosane : 5.97 min COMPOUND RRT COMPOUND RRT dimethylsulfone propoxyphene HCl amphetamine sulfate atropine sulfate methamphetamine cocaine HCl N,Ndimethylamphetamine tetracaine HCl phenylpropanolamine HCl triprolidine niacinamide tetracosane methylephedrine phenylbutazone MDA HCl codeine Phosphate 1.202
4 MDMA HCl morphine sulfate benzocaine diazepam MDEA hydrocodone bitartrate guaifenesin acetylcodeine acetaminophen monoacetylmorphine phenacetin oxycodone Base methylphenidate benzoylecgonine tartrate caffeine chloroquine phosphate carisoprodol heroin HCl ketamine HCl quinine base diphenhydramine HCl quinine HCl antipyrine quinidine HCl lidocaine HCl zolpidem doxylamine succinate papaverine aminopyrine clonazepam phenobarbital hydroxyzine xylazine alprazolam levamisole diltiazem dipyrone noscapine procaine HCl amoxycillin not soluble clenbuterol HCl creatine hydrate not soluble brompheniramine creatinine HCL not soluble dextromethorphan scopolamine HBr not soluble methadone HCl CAPILLARY ELECTROPHORESIS Method DXM-CE1 (for methorphan) Injection Solvent: 3.75 mm Sodium Phosphate ph 3.2 Standard Solution Preparation: Prepare standard solutions of dextromethorphan and levomethorphan at approximately 0.1 mg/ml using the above injection solvent. Sample Preparation: Prepare a sample solution so that the concentration approximates the standard concentration using the above injection solvent. If necessary, filter the sample with a 0.45µm filter prior to injection. Mode: Dynamically coated capillary CE
5 Column: Run Buffer: Detector: Voltage: CE standard Capillary 50 µm ID, 40 cm LEF Microsolve concentrate for d,l-methorphan: Dilute to 15 parts MeOH- 85 parts concentrate UV DAD: 200 nm Reference: 480 nm 20 kv Cassette Temperature: 15 C Precondition: Injection: Run Time: Typical Migration Time: Flush 1.0 min 0.1 NaOH Flush 1.0 min water Flush 1.0 min CElixir A Flush 2.0 min diluted Microsolve concentrate Pressure 35.0 mbar 2.0 sec sample vial Pressure 35.0 mbar 1.0 sec water 5 min Dextromethorphan: min Levomethorphan: min 4. SEPERATION TECHNIQUES N/A 5. QUANTITATIVE PROCEDURE 5.1. GAS CHROMATOGRAPHY Method DXM- GCQ-1 (for methorphan) Internal Standard Stock Solution (ISSS): 1 mg/ml of eicosane into CHCl 3 Standard Solution Preparation: Prepare a standard solution of methorphan at 1.0 mg/ml and dilute to volume with the ISSS. Sample Preparation: Accurately weigh an amount of sample into an appropriately sized volumetric flask so that the final methorphan concentration is approximately equivalent to that of the standard solution. Dilute to volume with ISSS. Instrument: Agilent 6890 Series II (or comparable) gas chromatograph operated in
6 split mode equipped with a FID detector Column: Carrier gas: 5% Phenyl/95% Methyl silicone gum 12 m x 0.2 mm x 0.33 µm film thickness Helium (constant pressure) Flow: 1.0 ml/min Temperatures: Injector: 280 C Detector: 280 o C Oven program: 1) 165 C initial temperature for 2.0 min 2) Ramp to 250 C at 30 C/min 3) Hold final temperature for 1.0 min Injection Parameters: Typical Retention Time: Linear Range: Split Ratio = 60:1, 1 µl injection Methorphan: 5.0 min Eicosane : 4.3 min mg/ml Repeatability: RSD less than 3% Correlation Coefficient: Accuracy: Error less than 5% COMPOUND RRT dimethyl sulfone amphetamine methamphetamine phenylpropanolamine ephedrine pseudoephedrine niacinamide MDA MDMA MDEA methorphan 1.00 caffeine ketamine 0.793
7 phencyclidine eicosane (ISTD) QUALITATIVE DATA 6.1. HIGH PERFORMANCE LIQUID CHROMATOGRAPHY MASS SPECTOMETRY Sample Preparation: Dissolve a small amount of sample into ammonium formate buffer and methanol. Filter sample with micron filter if necessary. Instrument: High performance liquid chromatograph equipped with diode array and mass spectrometer detector (Agilent 1100 Series SL or equivalent). Column: Phenomenex Hydro-RP column, 150 mm x 3.0 mm, 80A, 4 µm Temperature: 40 C Detector: Ionization Mode: Flow: UV DAD: 210 nm, 10 nm bandwidth Reference: 450, 100 nm bandwidth MSD: Scan Mode, single quadrupole with an electrospray ionization source Polarity: Positive Fragmentor: 160 V and 260 V API-ES Drying gas temperature: 350 C Drying gas flow: 13.0 L/min Nebulizer Pressure: 30 psi Capillary Voltage: 4000V Scan Range: m/z 0.50 ml/min Injection Volume: 2.0 µl Buffer:: 10mM ammonium formate ph 3.7 Mobile Phase: Typical Retention Time: 65% 10mM ammonium formate ph 3.7: 35% acetonitrile Dextromethorphan in 4.2 min See spectra on the following pages for LC-MS, FT-IR, FT-Raman, Mass Spectrometry, Nuclear Magnetic Resonance, and Vapor Phase IR.
8 7. REFERENCES E. G. C. Clarke, Modern identification of some modern analgesics, Bulletin on Narcotics, 11, No. 1, (1959). Charles C. Fulton, Modern Microcrystal Tests for Drugs, Wiley-Interscience, New York, ADDITIONAL RESOURCES Wikipedia
9
10 %T FTIR/ATR Dextromethorphan Hydrobromide 4 scans, 4 cm-1 resolution cm FTIR in KBr Dextromethorphan Hydrobromide 1 scan, 4 cm-1 resolution %T cm-1
11
12 %T Vapor Phase IR Dextromethorphan in Chloroform cm-1
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